Truth Or Dare
by CastielsKiss
Summary: Castiel Novak was living a normal life, as anyone would be having in the 20's especially since the war had just finished and New York city was basically a huge party everyday now. Gabriel and Castiel live together, Cas not having a well paying job and Gabriel's parents having kicked him out for liking men and women. Castiel goes out one night, only interested in the bartender.
1. Chapter 1

Castiel Novak had lived a very normal life, the first world war had just ended. It was almost unbelievable that the war was over, no one thought it was going to end so soon. All of New York city was just a huge party, throughout the entire day Castiel would pass a parties every other building. He wasn't the biggest fan of parties, to him they quite annoyed him after the first few days especially sincee his work place was celebrating practically singing Swanee by Al Jolson at the tops of their lungs every morning before the ships even came in. Castiel was the lad who unloaded the ships everyday before noon came rolling around.

He was never able to afford to dress fancy so he only had one nice suit that he saved for special occasions. Whereas his cousin, Gabriel, owned only suits. Gabriel and Cas lived together in a well built house just outside of the wild city, it was painted white, only one story, and a tiny garage that could barley hold Gabriel's car that they had built themselves once the first car came out, pledging to each other that they would get one as soon as they could afford it. Cas could barely afford anything, which was the only reason he was living with his cousin.

Gabriel always had someone new come over, sometimes men and sometimes women. Cas was always accepting of his cousin, especially since he was a queer himself, the only problem he had was that he had to sleep in the car sometimes, not wanting to listen to what sounds they had to offer. Gabriel was quite the whore, he liked to call himself classy whenever Cas would call him out for just being a cheap prostitute.

Cas slumped down onto the worn couch they found at a shitty furniture store just before the war began, when Castiel first moved in after just graduating college. That was almost five years ago now, Castiel remembering his birthday was coming up soon. The thought of throwing himself a party made him sick, he was still young, going to hit twenty four now so not throwing a party wouldn't matter. But if his cousin remembered his birthday then he'd be forced into a party.

"Hey!" Gabriel threw his entire bodies weight down onto the empty spot next to Castiel, making the couch groan as if it was going to snap in half. Cas just got relax just to have his nerves spike again. It wasn't always bad living with your cousin, even if he was a sex addicted asshole sometimes, he cared more for Castiel then any of his family had. "Whats gotchya down in the dumps?" Gabriel frowned, noticing Castiel was more stressed then usual.

"There's nothing to do anymore." He kept his head tilted back with his eyes closed. Gabriel looked at him in disbelief.

"Are you kidding me?" He pretty much shouted into Cas' ear. Cas winced and covered his ears. Gabriel threw his arm towards the door. "There is a party literally everyday! Everyone is careless, you could hook up with whoever you meet! How can you even say there is nothing to do?" He continued to shout, forcing Cas to roll over onto his side to face away from him.

"Gabriel, shut up!" Gabriel shut his mouth in anger, glaring at his younger cousin. He grabbed his arm and forced him to face him. Cas dropped his arms from the sides of his head.

"If you don't go out tonight then I'm kicking you out." Gabriel's eyebrows seemed like they were glued together now. "You're taking the car," He dropped the keys into Castiel's lap, "and you're going to go out and get wasted and bang some hot guy, do you understand?" Castiel looked down at his lap then back up at Gabriel, annoyed. Gabriel stuck his finger into his face, "If you don't come home tomorrow with a hangover, then I am never allowing you my food again."

Castiel gripped the keys and used Gabriel's shoulder to force himself off of the couch. He stared at the door for a second before spinning around and looking down at Gabriel, who had a smug smile on his face. "Where do you expect me to go, Gabriel?" He threw his hands up, about to slump back down when Gabriel jumped up and held his chest getting into his personal space.

"Listen! Listen!" Gabriel caught Cas' attention. "Listen," He took Cas' face in his hands so he would look at him properly. "There is this place called The Cotton Club, its about a block from the Harlem River. One of the biggest hot spots out there, I promise. The flappers dance all night, sharing kisses to entertain the men. Now I know you're a strict faggot, which is why I'm telling you about this place. Really late on Fridays, they have the Pansy performer." Castiel's face flooded with confusion. "Pansy performers are the gay flappers. I've gone to see them quite a few times." Gabriel winked, smiling a little remembering his times with Pansy performers.

Cas put his arms up. "Okay Gabriel, I don't want to hear any stories. I'll just go and check it out." Gabriel was almost jumping from happiness. "But I can't promise that I will get drunk because that isn't me, and you know that." Gabriel scuffed and started pushing Castiel towards his bedroom door, forcing Castiel to change into something better looking, basically telling him to put on his nice suit for his nice day out. Gabriel sat on the edge of Cas' bed as he changed quickly, feeling extremely uncomfortable with his own cousin watching him get undressed, but Gabriel seemed to be the happiest person alive, seeing his closest family member who never did anything finally do some.

It didn't take Cas long to change, especially with Gabriel closely watching him. He slipped a vest over his tucked in white shirt and pure black suspenders, wanting to be fancy but not to fancy. He buttoned the two buttons as Gabriel pushed a nice grey coat over his shoulders, just before jumping in front of him and tying a bow tie around his neck saying how much men likes bow ties more then regular ties. Just as Cas was was about to grab his hat, Gabriel threw him towards the door, pushing his entire body weight to the front door almost like he was planning on having an orgy instead of just bringing one person home. With Cas having the car, Gabriel had no way to pick anyone up.

Castiel didn't even turn around as he exited the door, he couldn't admit how badly he wanted to have fun he just didn't know where, or what to do. Once Gabriel mentioned The Cotton Club his attitude perked instantly. His street was empty, he didn't live on a very rich street which meant the neighbors were either working over-time for more pay that they would never get or they were trying to keep quiet about smuggled alcohol. That was how Gabriel was, even when he went out, he was still very careful with what he was doing. Smuggling alcohol was almost a hobby to him now.

Castiel wasn't very bothered with it, it just gave him another reason to not speak with people he didn't know. He didn't bother looking around before pulling the garage door up, holding it up until he heard a click that ensured it wasn't going to fall down the second he removed his hands. He pulled the door open forcefully, knowing it got stuck due to how often Gabriel complained about it.

He stuck the key in and started the car as if it were a fluid movement. It took a few revs before it started though. It was only the first of its kind which meant it was going to be quite shitty, but the fact that it was even invented made Castiel's life so much easier. The thought of him having to walk to the club, that was sitting in Harlem, made a flash of fear wash over Cas. He casually shrugged it off and pushed on the gas pedal.

It didn't take long to get to the club, the only problem Cas had was having to not hit random drunks running around in the streets. Those people being chased down by police was the moment entertainment Castiel had gotten the entire month.

He rolled up to the club not long after. He parked on the side of the street, the parking lot was completely full and so was most of the street. He figured it was still quite early so the flappers must still be there. He killed the engine and closed his eyes, rubbing them hard before relaxing into the seat a little. This was the first time he's gone to a club, let alone ready to hook up with someone. He checked his watch, it was barely 7:30 at night which told him the flappers were going to be around for at least another hour seeing as sunset wasn't until 8:30 and no one really flaunted about how they were queer, a lot of the queer men in town were married to women and have had children with them not being able to come out because most were needed in the war and if anyone were to find out fags were fighting, oh you bet your ass dead within a few days.

Cas decided he wasn't going to brood in his car and pulled himself together, pushing the door open and stepping out. He had a lot more confidence in the clothing he was wearing now then he did in his previous work outfit that made him look like a raggedy man that you couldn't approach because he'd try to start a fight with you.

Castiel wasn't the type to be pro-war, he was very much against fighting but his little opinion wasn't going to change anything in the world, especially since probably no one else would agree with him. He kept his opinions to himself and that was how it always was.

He slammed the door shut, dropping his keys into his pants pocket, and began walking towards the club. He noticed some men hiding underneath tall collars and hats as if they were embarrassed to be there. Cas didn't mind much, he didn't really know anyone in New York so he wasn't afraid to show himself. Besides, right now the club just had women dancing around half naked to some Willy Smith record he'd never heard before. What was so shameful about that? Men loved the women's body, Cas couldn't understand why, but they did.

He pushed open the club door entrance, being greeted with the strong scent of sweet rose perfume and smooth jazz liquefying into his eardrums. Most of the smell came from down in the basement that was awfully hidden almost next to the main entrance. The first floor was just performers no one knew about and men trying to get food shoved down their throats. This floor wasn't very appealing, but it was a good enough cover to not get found out about their smuggled goods.

Castiel had to force himself to open the door and walk down the freely old staircase, terrified it was going to break any second now under his weight. Of course the fact that many flappers were growing increasingly large and they had to travel those stairs every time they had a show. Cas convinced himself that thought would mean it wasn't going to break under him which was the only reason he made it to the bottom without gripping the over used railing.

Once he got to the bottom his eyes were greeted with many women bottoms, more then Cas' comfortable amount; 0. But, as he expected, the flappers were still going for the unnaturally horny men who cat called and wolf whistles every time the showed even a little bit of skin. It almost made Cas physically sick seeing all these men pretty much kissing the feet of these women just for a peek at her covered breasts.

He made his way over to the cleared bar, hoping to get a drink he'd like. As he took his seat a taller tanish man walked over, leaning over the counter. He was wearing black dress pants, light blue suspenders, and a white buttoned shirt with the top three buttons open and the sleeves rolled up just below his elbows. Cas didn't even notice he was talking, more then obviously to distracted with his thick forearms and green eyes and that illegally beautiful smile.

"What?" Cas blurted, shaking the thoughts of the man spooning him or possibly becoming the guys bitch, realizing the guy could be just another douche bag who works behind the counter.

He chuckled a little, keeping that drop dead grin on his face. "I asked if you wanted something to drink." Cas looked down at his hands laying together on the bar table, embarrassed.

"Uh yeah, could you make a Bronx?" He was almost to scared to ask, knowing it was more on the womens side of drinks. But he couldn't help himself, that was one of his favorite mixes and it got him drunker faster. He desperately wanted to loosen up before the pansy performers came in.

The man behind the counter smiled and flipped a cup up onto the table, putting in the gin and vermouth mixing it quickly before pouring a little bit of orange juice into it, stirring it quickly and leaning onto the table putting his face closer to Cas'. "Would you like an umbrella?" He was obviously being sarcastic, pushing the cup towards him. He dropped a thin straw into the drink before pushing himself up, not taking his eyes off of Castiel.

Cas mumbled a thanks before taking the straw into his mouth and taking a long suck, swallowing the drink down each time his mouth got full until he was out of breath. He took a moment to scan around the room, the music wasn't as loud as he expected seeing as he could hear the bartender over the music without asking him to speak up. It didn't look like the women were going to be finishing anytime soon so he turned back to his drink and began sucking it up again.

He failed to notice the few men sitting at the bar, all sitting quite a ways apart as if they were afraid of being recognized. The bartender had nothing better to do so he made his way over to Castiel, actually curious about who he was.

He leaned over the table once more. "So, you new here?" Cas tried his best to not get distracted with the mans bright green eyes. Without saying a word, he nodded, almost afraid of making conversation with the guy. "You here for the fag show?" Cas' face burned red, causing Dean to show his teeth. "I take that as a yes, so are you a fag yourself?"

Cas looked up from his drink slowly, almost afraid of how he'd react if he said yes. The guy chuckled, "Its alright if you are, I am so I would understand." Cas coughed, choking on his drink as the guy laughed at him.

"I uh..." Cas spun his straw around the perimeter of his cup, swishing the ice silently. "Yeah, I've never been here but uh, my cousin comes here a lot I guess..." The bartender looked surprised for a few seconds before his face relaxed again. "His name is uh, Gabriel. I guess he's only come on Friday nights a few times but he spends his time here pretty much everyday I guess... I don't know, we don't talk often."

"Well I only work here on Friday nights," The guy pointed to the flappers. "The women don't talk to me due to the fact I'm a fag, but the pansies love me." He sent a warming smiled in Castiel's direction, which made him relax better then he had all night. "I only work Fridays because the boss couldn't find any fag who would work here only on Friday nights. You see, the economy is crashing but no one realizes it because everyone's head is full of the idea that the war being over means everything is perfect now." He leaned in closer to Cas, not wanting to be overheard by the passersby.

Cas has never spoken about his thoughts on the economy to anyone, not even his cousin, which was the only person in his family that he was close with. This man was just sitting there blurting out his feelings to Cas, who was a complete stranger, and Cas has never been so comfortable in his entire life. A smile slowly spread across his face as the man continued on with his rant about how shitty the economy was right now until Castiel interrupted.

"Whats your name?" The guy stopped mid-sentence before closing his mouth and giggling almost, holding his hand out now standing up straight.

"I'm Dean, Dean Winchester. You are?" He obviously liked it formal. Cas took Deans hand and shook it carefully as if he was afraid of breaking him.

"Castiel Novak, but you can call me Cas."

"Nice to meet you Cas, I must've been boring you with my rant. I'm sorry about that, by the way." Cas shrugged, pushing away his now empty drink. "Would you like another one?" Dean offered, pointing at the glass.

"No thanks, I'm driving home tonight." Dean smirked at Cas as if he thought differently.

"Well thats no fun." Dean was so engulfed in the rant before that neither of them even noticed the club start to empty and then fill up again. "Looks like the flappers are gone, guess its time for the pansies." He had the biggest smile Cas had ever seen on his face. He leaned down again, getting close to Cas so no one else could hear him. "The first pansy thats going to come out, his stage name is Ginger Tonic. He goes by that because he doesn't want anyone to find out his real name which I can understand, who wants to know when there is a fag in the family, right?"

Castiel was getting sick of hearing the word fag being used but, as far as anyone knew, there was no proper way to address a queer. He looked at the low stage, waiting for this Ginger person to walk out. "He gave me my first blow job." Dean winked, Cas' face got hotter then it ever was. Dean laughed and watched the stage with him as if they were best friends.

The room dimmed and the song 'Five Foot Two, Eyes of Blue' by Gene Austin began to play all around them. Cas could feel his heart rate quicken, excited to see what they had to offer. A tall man strutted out, his figure completely black, but Cas still felt like he knew the man just by the way his body was built.

Once the singer of the song started to sing, the lights flashed on to reveal Balthazar, Castiel's older brother.


	2. Chapter 2

Cas couldn't look away from his older brother. He was wearing a floral, red flappers dress and sparkling flats. Most women couldn't afford heels unless they got a very high amount of money. Castiel's mouth gaped open mindlessly. Dean smiled to himself a little, more reliving the memory instead of wanting more from him.

"You okay, Castiel?" Dean was rubbing finger prints off of a new glass while Cas continued to gape. "He is quite the sucker." Dean winked and Cas almost gagged. "I paid a lot of money for him, he insists he isn't a fag but why would he have sucked my dick if he wasn't?" Dean shut it mouth now, terrified Cas was annoyed with him, but he truly wasn't. Cas quite liked Dean, but knowing his older brother sucked him off made him uneasy.

"No..." Cas finally said, Dean lifted his head and looked at him.

"Hmm?"

"He insists he isn't a fag because father would kill him." Cas rolled his head to look at Dean again, his eyes wide. He looked at Balthazar slowly then back at Cas, opening his mouth, closing it, then opening it again.

"O-oh..." Dean stutter, looking back down to the glass he was gripping tightly onto. A nervous laugh dropped off of Castiel's tongue like sweet honey. After a long silence, Dean finally spoke, not looking at Balthazar anymore. "Do you want another drink because I could really go for one right now." Dean's laugh was even more awkward then Cas' was, but Cas didn't care.

He nodded without saying a word. Instead of two big drinks, Dean brought over two shot glasses and filled both up to the rim. "To being a fag." Dean smiled as if it would erase Balthazar from Cas' memory. Cas smiled and clinked their glasses together, tipping his head back instantly swallowing it down faster then Dean. He slammed the glass upside down onto the counter, Dean copying shortly after.

"Two more." Cas wanted to get piss drunk and have sex tonight. Even if the alcohol burned his tongue and made his stomach hurt, he didn't care. He wanted his mind to not care either. Dean nodded and brought over two more. They followed the same motion as before, ordering even more.

Cas wasn't able to stand up after a few shots, Dean seemed just fine. Was he even drinking? Cas watched him drink each one, couldn't really fake that. Cas was giggling at nothing while he ordered another.

Once that one was down he became talkative. "Can I become the behind counter person?" He slurred happily watching Dean through slightly blurred vision. Dean smiled widely, waving him around to the little parting in the counter that allowed the employes in and out from behind the counter. Cas walked over eagerly, going to where Dean was standing before.

Cas' eye's got wide as he looked around, apparently amazed at how much alcohol was stored behind a bar. He bite his bottom lip and eyed Dean secretly. Dean was leaning over the counter writing down something Cas couldn't see before stuffing it into his pocket and starting to clean up the glasses they used.

"You know," Dean's voice made Cas jump and turn around with a terrified look on his face which caused a fit of giggles from Dean.

"You scared me!" Cas shouted pointing at Dean before his bending over in laughter. Dean forgot what he was going to say as he watched Castiel's face while he laughed, thinking about how badly he wanted to hold it and just kiss it everywhere.

Dean put his hand onto Cas' arm, running it slowly down to his hip. Cas was up straight again, giggling but watching for what Dean's next moves were going to be.

Dean looked around the bar, no one seemed to be near the bar and they haven't been near it since the Pansy Performers began. Dean bit his lip to keep the smile down, pulling Cas' body close to his. "Follow me..." He whispered into his ear, sending shivers down Cas' spine before he nodded vigorously, excited for what Dean was gonna do.

Dean entangled their fingers before turning around and brought Cas to the back, constantly checking behind him in case someone was going to follow them. Yeah the bar had essentially turned into a gay bar for the night, no one would admit to being queer. Dean slammed the door, eager to get Cas.

He pushed Cas against the wall, Cas watched him almost scared. The room was dark but they could still see each other.

"What are ya gonna do...?" Cas whispered, neither could look away from the others eyes as they stood there pushed against each other.

"Are you single?" Dean asked bluntly, not really caring if he was or not. Luckily, Cas nodded quickly. "Good." Dean mumbled, pushing his mouth against Cas'. It took Castiel a minute to realize what was going on before he closed his eyes and melted into the kiss.

Dean's hands were wandering around Cas' lower stomach, teasing him more then he needed to get hard. Cas moaned into Dean's mouth, blocking out the sounds coming from the bar. Dean rubbed their hips together harder then intended making Cas pull away and half yell. Dean hushed him quickly, not wanting to get caught.

Cas whimpered and chewed his lip before Dean forced another kiss in. Dean was pinning Cas to the wall but not strong enough. Cas pushed hard against Dean's groin from outside of his pants, gripping it tight enough to cause him to possibly come. He groaned and his body went weak, Cas took this time to force Dean against the wall wanting a turn.

Dean looked down at Cas, eyes half open from the pleasure Cas was giving him by squeezing lightly every once in a while. "You like to make me your bitch, Cas?" Dean moaned and Cas grinned widely hearing Dean say his nickname.

"Maybe sometimes..." He brushed his lips against Dean's jawline, nipping at his collar lightly licking it after. They fought for dominance for awhile before Cas finally pulled away, breathlessly.

They stood there for what felt like forever before Cas finally looked up at Dean. "Lets go." He tugged Dean impatiently towards to door.

"Where are we going?" Dean wouldn't budge, making Cas angry.

"My place, lets go." Dean smiled widely and followed quickly, getting into Cas' car without hesitation.

They couldn't wait though, Dean unzipped Cas' pants and started to pump his cock causing Cas to lean his head back and moan almost swerving into the other lane. Dean smiled to himself and let go of Cas, moving closer to him and kissing him hard against the neck. Cas started touching himself a bit, not wanting to wait.

He finally couldn't take it anymore and pulled over, fixing his pants. Cas jumped out of the car and tried to run to the other side where Dean was sitting. As he wrenched the door open Dean got the clue on what they were doing.

He leaned the chair back, stripping from his pants quickly. Cas left his own on the side of the road not even caring. He left the door open as he sat on top of Dean's lap, rolling his hips receiving hard moans from Dean, only to make Cas harder.

Dean gripped Cas' thighs to make him stop. "Ride me, baby." Dean's voice was lower then usual, and a lot sexier then usual. Cas almost fell out of the car and he pushed his briefs off, Dean mimicking.

Before Cas got back on top of Dean, he wrapped his mouth around Dean's cock to make it wet, wanting to be able to walk the next morning. Just as Cas pulled his mouth away, pre-cum came out and Cas couldn't help but rub that all over his.

Dean was ripping his lips open, dying for Cas to ride him. Cas was finally happy with himself, holding himself just above Dean's body, pushing his mouth against Dean's and slowly forcing Dean into him. Whimpering a little from small pains not being used to it anymore. Dean gripped Cas' ass so he wouldn't hurt himself.

The second he was on top completely, he started riding him faster and faster ignoring the pain as he got used to it. Dean's hips bucked up a few times making Cas scream out in pleasure. He started chanting 'I'm gonna cum' into Dean's ear making Dean slam his hips up hard.

Their orgasms were in sync, Dean just moaning a little whereas Cas was screaming Dean's name. He slowly pulled out and slumped down on top on Dean, not wanting to move what-so-ever.

"Would you like to come and stay with me tonight?" Dean mumbled, running his fingers through Cas' soft hair. Cas' mouth curled up a little, his eyes closed. He nodded against Dean's chest, and Dean gently pushed himself out from under Castiel's body, pulling his pants up and closing the door as he made his way over to the other side.

Cas knew Gabriel was going to be worried, more pissed of then worried especially since he was letting someone who was a complete stranger drive around in his car. But frankly, Cas didn't give a single shit. Gabriel told him to go out and have fun, or something like that Castiel's mind was blanking itself in several places right now because of the impact of the orgasm and how much alcohol he'd drunk. Gabriel was probably going to pissed about that too, I mean he gave Castiel permission didn't he?

Cas didn't care about anything right now. He didn't care that he'd abandoned his parents or that they looked down on him for living with Gabriel, as Gabriel came out just a year before Cas moved in. He didn't care that he just met some guy at a bar, who happened to have gotten a blow job from his older brother who disappeared for awhile, and then fucked him in the passenger seat with the door wide open while he screamed out Dean's name.

He wished everyday he could be this careless, of course that was a lot to ask for.

He just really didn't care anymore.

He fell asleep that night to the sound of the engine and road under his feet, having never felt so blissful his entire life.


End file.
